1,4-Dibromobenzene → HCID 57420154, Verbindung

HRID 1619211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619211
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[N:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2([OH:26])[CH2:22][CH2:21][N:20]([C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:14]=3)[CH2:25][CH2:24]2)=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 78041,4-DibromobenzeneHCID 14788561-Pyrimidin-2-yl-piperidin-4-oneHCID 178418339Butyllithium

Produkt 1

HCID 57420154HCID 57420154, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1,4-dibromobenzene (213.3 mg, 0.904 mmol) in THF (4 ml), was added n-BuLi (2.5 M in hexanes, 0.362 ml, 0.904 mmol) at −78° C. After being stirred for 30 minutes at the same temperature, a solution of 1-pyrimidin-2-yl-piperidin-4-one (80 mg, 0.452 mmol) in THF (3 ml) was added. The mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with addition of water (10 ml) and EtOAc (50 ml). The organic layer was washed with brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (40% EtOAc/hexanes) to give 4-(4-Bromo-phenyl)-1-pyrimidin-2-yl-piperidin-4-ol as a colorless oil (140 mg, 93%): 1H NMR (CDCl3, 400 MHz) δ 8.33 (d, J=6.4 Hz, 2H), 7.47 (d, J=12.0 Hz, 2H), 7.41 (d, J=12.0 Hz, 2H), 6.49 (t, J=6.4 Hz, 1H), 4.72 (m, 2H), 3.40 (m, 2H), 2.05 (m, 2H), 1.78 (m, 2H); MS calc'd for C15H17BrN3O [M+H]+: 335; Found: 335.

Aufarbeitung

  1. stirringstirred for 1 hour
  2. customThe reaction was quenched with addition of water (10 ml) and EtOAc (50 ml)
  3. washThe organic layer was washed with brine (5 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto furnish the crude product
  8. customThis material was purified by column chromatography (40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ef881fcb6d9f492c877325aeac9beb88
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772291B2

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